Ben Cherington is both the luckiest and unluckiest man alive right now.
He's just been handed the big $400 million lottery check and he gets to spend the money on anything he wants.
Need $150 million for starting pitching? No problem.
Need $300 million for a certain superstar slugger? We got that.
Being the GM of a team like Boston has certain challenges; money isn't one of them.
Cherington will be desperate to distinguish himself from Theo Epstein and will be working quickly to make a signature move for the 2012 season.
This is where the unlucky part of the equation comes into play.
Every move Cherington makes is going to be scrutinized and compared to the great Theo Epstein. The man who brought Boston two World Series championships.
What if he gives Albert Pujols 10 years and $300 million and Pujols turns into post-Seattle Ken Griffey Jr.?
Something like that will define Cherington's entire career as a GM.
Let's take a look at five players that I think he'll target this offseason.